We recently had the chance to connect with Olivia Castaldy and have shared our conversation below.
Hi Olivia, thank you for taking the time to reflect back on your journey with us. I think our readers are in for a real treat. There is so much we can all learn from each other and so thank you again for opening up with us. Let’s get into it: What do the first 90 minutes of your day look like?
I’m very intentional about slow mornings, especially as someone who works from home. Creating a clear separation between work and home life can be challenging, but it’s something I prioritize deeply.
I start my day using my Hatch Alarm, which allows me to ease into the morning without immediately reaching for my phone or other devices. From there, I get ready for the day (comfortable work-from-home clothes with a polished top is my go-to) then take care of my dogs, Rocky (Doodle) & Flora (Husky).
After that, I usually spend some quiet time with my fiancé. That often looks like sharing a cup of tea and breakfast, either catching up on our favorite reality TV or simply sitting in silence before the day’s chaos begins. If I’m lucky, I’ll fit in a walk or light movement, though I’m typically more of an evening workout person.
I’ve also built boundaries into my schedule to protect these slow starts. Two days a week my calls begin between 8–10 a.m., but the rest of the week I don’t take calls until after 11 a.m. It’s a small but powerful way to reinforce intentional mornings and start my days feeling grounded rather than rushed
Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Olivia Castaldy, and I’m the Founder and Marketing Director of OCM Digital Marketing, a Colorado-based marketing agency built to support small businesses, start-ups and purpose-driven brands through thoughtful, results-oriented strategy. I’m a Colorado State University alum, and the entrepreneurial, community-first spirit of Northern Colorado has played a major role in shaping both my career and my approach to marketing.
I bring over a decade of experience working across both B2C and B2B marketing, partnering with more than 50 brands to strengthen their digital presence, clarify their messaging, and build marketing systems that actually drive growth. I began my career in Small Business Incubation and Economic Development, where I worked closely with founders and early-stage companies, an experience that gave me a deep appreciation for the realities of building and scaling a business and reinforced my passion for supporting entrepreneurs.
What makes my work especially meaningful is the intersection of strategy and community. Beyond leading OCM Digital Marketing, I’m deeply committed to giving back and supporting underrepresented founders, particularly women and minorities within the cannabis industry. I’m also the founder and host of The Women in Cannabusiness podcast, where I highlight the stories of women shaping the industry, fostering connection and education while helping challenge long-standing stigma.
Whether through my agency, the podcast, or local community initiatives, my work is rooted in helping founders feel supported, seen, and set up for long-term success. Colorado’s collaborative, entrepreneurial culture continues to influence how I work, who I partner with, and the kind of impact I aim to create.
Great, so let’s dive into your journey a bit more. Who saw you clearly before you could see yourself?
My very first internship supervisor, Renee Younes, at the Mason Enterprise Center–Fauquier, saw me clearly long before I fully saw myself. I was a young teenager in my hometown with big ambition and a deep curiosity for business, and Renee immediately recognized both.
During the internship, she encouraged every intern to create something meaningful. What I created became a youth forum called FUTURE, a monthly networking-style event for teenagers and young adults ages 14–21, where local business owners shared their stories of how they built their careers. Growing up in a small town, I saw how easy it was for young people to develop limiting beliefs about what was possible for their futures. I wanted to create a space that showed my peers that they weren’t confined to one path, that ambition, creativity, and hard work could open doors.
Renee supported the idea wholeheartedly and walked beside me every step of the way. She showed me how to build community, leverage local resources, and believe that my voice mattered. She even brought me to my very first networking event, a Fauquier Chamber of Commerce luncheon where I felt wildly out of place. Instead of letting me fade into the background, she introduced me to key figures in the community and gave me the confidence (and the opportunity) to speak for 30 seconds in front of more than 150 people to promote my program.
Beyond professional mentorship, Renee modeled what real leadership looks like. She taught me how to be a compassionate manager, how to lead with empathy, and how to support people through hard days. When things felt heavy, she didn’t pile on pressure… she’d say, “Let’s get out of here and go for a walk and grab a coffee.” She made space for me to be human while still believing in my potential.
She used to come into the office after watching Shark Tank and tell me that some of the kids on the show reminded her of me, and that I was going to do big things. That belief stayed with me. Moving to Colorado and building my own agency wouldn’t have been possible without Renee’s guidance, trust, and unwavering belief in who I could become.
When did you stop hiding your pain and start using it as power?
I stopped hiding my pain and began using it as power when I chose to step into the cannabis industry openly and unapologetically.
In high school, I was diagnosed with anxiety and clinical depression and was prescribed antidepressants and benzos at just 16 years old. At the time, cannabis was illegal in Virginia, but there was growing awareness in states like Colorado, California, and Oregon around its medicinal benefits. Having already experienced cannabis recreationally, I made a conscious decision to explore it as an alternative to prescription medication, something that ultimately changed the trajectory of my life.
That choice led me to move to Colorado for my undergrad, where I focused on building a healthier lifestyle with not only cannabis but the outdoors. Over time, I lost more than 50 pounds and was able to come off pharmaceutical medications entirely… a shift that has lasted nearly a decade. What once felt like something I had to hide became something I deeply believed in.
Ironically, the stigma followed me early on. In high school, I was investigated for being under the influence of cannabis at a school sports game after a “friend” reported me. At the time, I joked that I’d one day “market weed.” Years later, that joke became reality.
Instead of letting shame or stigma define me, I chose to turn my experience into purpose. Working in the cannabis industry allowed me to reclaim my story, advocate for education and access, and build a career rooted in authenticity. What once felt like pain became a source of clarity, confidence, and direction, and ultimately the foundation for the work I do today.
I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. What would your closest friends say really matters to you?
My closest friends would say that building community truly matters to me. Whether it’s through the cannabis industry with my podcast, The Women in CannaBusiness, or through local initiatives like organizing craft nights, game nights, or my local cookbook club, bringing people together is at the heart of everything I do.
Community has always been important to me. My parents love to joke that when I was three years old, I would walk around our neighborhood offering the other kids hot dogs and asking them if they wanted to play, older, younger, it didn’t matter to me. I just wanted people to feel included and connected.
That instinct has followed me into adulthood. I’m deeply fulfilled by creating spaces, both professionally and personally, where people feel welcome, supported, and seen. Whether it’s through storytelling, shared meals, or meaningful conversations, gathering people together is how I build relationships and how I measure success.
Okay, we’ve made it essentially to the end. One last question before you go. Could you give everything your best, even if no one ever praised you for it?
Yes, and I think that’s something I learned early on without realizing it. Growing up, I was never particularly good at sports. I wasn’t competitive in the traditional sense, and for a long time I thought that meant I just didn’t have that drive. What I eventually realized is that I had simply grown accustomed to putting in effort without receiving much recognition, and to failing without letting it define me.
That experience taught me not to fear failure or depend on external validation to keep going. In hindsight, that mindset has been one of my greatest strengths as an entrepreneur. Building something from scratch requires consistency, resilience, and belief long before there’s praise, traction, or visible success.
I’ve learned to give my best because the work matters to me… not because someone is watching or applauding. And that ability to keep showing up, especially when no one is cheering yet, is what I believe makes a great entrepreneur.
Contact Info:
- Website: https://ocmdigitalmarketing.com
- Instagram: https://www.instagram.com/ocm_digitalmarketing
- Linkedin: https://www.linkedin.com/company/ocmdigitalmarketing/
- Facebook: https://www.facebook.com/ocmdigitalmarketing/
Image Credits
Personal Photo / Headshot — https://danjabarberphotography.com/
Supplemental Photos / Branding Shoot — https://www.lcphotostyle.com/
